JPH0680113B2 - 芳香族ポリマ−の製法 - Google Patents
芳香族ポリマ−の製法Info
- Publication number
- JPH0680113B2 JPH0680113B2 JP59501652A JP50165284A JPH0680113B2 JP H0680113 B2 JPH0680113 B2 JP H0680113B2 JP 59501652 A JP59501652 A JP 59501652A JP 50165284 A JP50165284 A JP 50165284A JP H0680113 B2 JPH0680113 B2 JP H0680113B2
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- polymer
- formula
- reaction
- lewis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229920000642 polymer Polymers 0.000 title abstract description 123
- 239000000178 monomer Substances 0.000 claims abstract description 78
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 39
- -1 poly(carbonyl-p-phenylene-oxy-p-phenylene) Polymers 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 19
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 6
- 239000002841 Lewis acid Substances 0.000 claims description 64
- 150000007517 lewis acids Chemical class 0.000 claims description 64
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 52
- 150000007527 lewis bases Chemical class 0.000 claims description 50
- 239000002879 Lewis base Substances 0.000 claims description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- 150000004820 halides Chemical class 0.000 claims description 33
- 239000003085 diluting agent Substances 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 239000012429 reaction media Substances 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 12
- AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 claims description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 11
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 8
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- UVGPELGZPWDPFP-UHFFFAOYSA-N 1,4-diphenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 UVGPELGZPWDPFP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005703 Trimethylamine hydrochloride Substances 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 239000002685 polymerization catalyst Substances 0.000 claims description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 5
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- BSILAEQTGTZMIW-UHFFFAOYSA-N bis(4-phenoxyphenyl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BSILAEQTGTZMIW-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- AMFMJCAPWCXUEI-UHFFFAOYSA-M 1-ethylpyridin-1-ium;chloride Chemical compound [Cl-].CC[N+]1=CC=CC=C1 AMFMJCAPWCXUEI-UHFFFAOYSA-M 0.000 claims description 2
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 2
- WCFDSGHAIGTEKL-UHFFFAOYSA-N n,n-dimethylmethanesulfonamide Chemical compound CN(C)S(C)(=O)=O WCFDSGHAIGTEKL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 2
- ATHHXGZTWNVVOU-VQEHIDDOSA-N n-methylformamide Chemical group CN[13CH]=O ATHHXGZTWNVVOU-VQEHIDDOSA-N 0.000 claims 1
- 229920000412 polyarylene Polymers 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 39
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 15
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000011968 lewis acid catalyst Substances 0.000 abstract 1
- 229920001470 polyketone Polymers 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 125000004104 aryloxy group Chemical group 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910001873 dinitrogen Inorganic materials 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000007086 side reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000029936 alkylation Effects 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- ITVUPWDTDWMACZ-UHFFFAOYSA-N (4-phenoxyphenyl)-phenylmethanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 ITVUPWDTDWMACZ-UHFFFAOYSA-N 0.000 description 5
- 238000003825 pressing Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920006158 high molecular weight polymer Polymers 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JKFWKYCRXYOPRC-UHFFFAOYSA-N [4-(4-phenoxyphenoxy)phenyl]-phenylmethanone Chemical compound C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1C(=O)C1=CC=CC=C1 JKFWKYCRXYOPRC-UHFFFAOYSA-N 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 230000000415 inactivating effect Effects 0.000 description 2
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010128 melt processing Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FIPTYOFKSOWKTF-UHFFFAOYSA-N 1,2-diphenoxybenzene Chemical compound C=1C=CC=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 FIPTYOFKSOWKTF-UHFFFAOYSA-N 0.000 description 1
- NBGFVPWSVYHCCW-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)phenyl]-2-[2-[4-(benzenesulfonyl)phenyl]phenoxy]benzene Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)OC1=C(C=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C1=CC=CC=C1 NBGFVPWSVYHCCW-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000007350 electrophilic reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XGFJCRNRWOXGQM-UHFFFAOYSA-N hot-2 Chemical compound CCSC1=CC(OC)=C(CCNO)C=C1OC XGFJCRNRWOXGQM-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48108383A | 1983-03-31 | 1983-03-31 | |
| PCT/US1984/000465 WO1984003891A1 (en) | 1983-03-31 | 1984-03-29 | Preparation of aromatic polymers |
| US481083 | 1990-02-16 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5279385A Division JPH06263871A (ja) | 1983-03-31 | 1993-11-09 | 芳香族ポリマーの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60500961A JPS60500961A (ja) | 1985-06-27 |
| JPH0680113B2 true JPH0680113B2 (ja) | 1994-10-12 |
Family
ID=23910522
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59501652A Expired - Lifetime JPH0680113B2 (ja) | 1983-03-31 | 1984-03-29 | 芳香族ポリマ−の製法 |
| JP5279385A Pending JPH06263871A (ja) | 1983-03-31 | 1993-11-09 | 芳香族ポリマーの製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5279385A Pending JPH06263871A (ja) | 1983-03-31 | 1993-11-09 | 芳香族ポリマーの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| EP (3) | EP0243997B1 (de) |
| JP (2) | JPH0680113B2 (de) |
| AT (2) | ATE41667T1 (de) |
| AU (1) | AU566373B2 (de) |
| BR (1) | BR8406499A (de) |
| CA (1) | CA1244996A (de) |
| DE (2) | DE3485955T2 (de) |
| GB (3) | GB8408082D0 (de) |
| IL (1) | IL71422A (de) |
| WO (2) | WO1984003891A1 (de) |
| ZA (1) | ZA842420B (de) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191839B1 (de) * | 1984-08-20 | 1988-12-14 | RAYCHEM CORPORATION (a Delaware corporation) | Arylätherketoncopolymere |
| US4808693A (en) * | 1984-08-20 | 1989-02-28 | Raychem Corporation | Aryl ether ketone copolymers |
| ES8704521A1 (es) * | 1984-09-06 | 1987-04-16 | Raychem Corp | Metodo de preparacion de una poli(arileno eter cetona) |
| ES8702932A1 (es) * | 1984-10-11 | 1987-02-01 | Raychem Corp | Metodo para preparar una poli(eter cetona) aromatica |
| ES8700677A1 (es) * | 1984-10-11 | 1986-11-16 | Raychem Corp | Metodo para la preparacion de un oligomero de arileno cetonao arileno sulfona |
| DE3542481A1 (de) * | 1984-12-11 | 1986-06-19 | Mitsubishi Chemical Industries Ltd., Tokio/Tokyo | Verfahren zur herstellung aromatischer polyketone |
| US4816556A (en) * | 1985-02-22 | 1989-03-28 | E. I. Du Pont De Nemours And Company | Ordered polyetherketones |
| CA1246297A (en) * | 1985-03-11 | 1988-12-06 | Robert A. Clendinning | Process for preparing poly(aryl ether ketones) |
| US4693851A (en) * | 1985-04-09 | 1987-09-15 | Raychem Corporation | Purification of acid halides |
| CA1272840A (en) * | 1985-06-03 | 1990-08-14 | The Dow Chemical Company | Method for making polyesters, polyamides and polyketones |
| US4720537A (en) * | 1985-11-25 | 1988-01-19 | E. I. Du Pont De Nemours And Company | Branched copolyetherketones |
| US4704448A (en) * | 1985-11-25 | 1987-11-03 | E. I. Du Pont De Nemours And Company | Copolyetherketones |
| US4841013A (en) * | 1986-09-18 | 1989-06-20 | Raychem Limited | Preparation of poly(arylene ether ketones) |
| DE3789354T2 (de) * | 1986-11-20 | 1994-08-04 | Asahi Chemical Ind | Aromatischer Polyether und Verfahren zur Herstellung eines Polyethers. |
| US4855387A (en) * | 1987-07-09 | 1989-08-08 | Raychem Corporation | Poly(arylene ether ketones) having biphenylene-4,4'-dicarbonyl groups |
| US4826947A (en) * | 1987-07-09 | 1989-05-02 | Raychem Corporation | Preparation of poly(arylene ether ketones) |
| JPH07103236B2 (ja) * | 1987-09-01 | 1995-11-08 | 三菱化学株式会社 | 芳香族ポリ(チオ)エーテルケトンの製造方法 |
| GB8726884D0 (en) * | 1987-11-17 | 1987-12-23 | Raychem Ltd | Poly(arylene ether ketones) |
| DE3829520A1 (de) * | 1988-08-31 | 1990-03-01 | Basf Ag | Verfahren zur herstellung von polyarylenetherketonen |
| DE3906178A1 (de) * | 1989-02-28 | 1990-08-30 | Basf Ag | Verfahren zur herstellung von polyaryletherketonen durch elektrophile polykondensation |
| DE3907027A1 (de) * | 1989-03-04 | 1990-09-13 | Basf Ag | Verfahren zur herstellung von polyaryletherketonen durch elektrophile polykondensation |
| US5227455A (en) * | 1989-12-14 | 1993-07-13 | Basf Aktiengesellschaft | Polymer granules having improved processability |
| TW256843B (de) * | 1992-06-11 | 1995-09-11 | Hoechst Ag | |
| DE4424039A1 (de) * | 1994-07-11 | 1996-01-18 | Basf Ag | Amphotere Metalloxide als Cokatalysator bei der elektrophilen Synthese von Polyaryletherketonen |
| DE4424042A1 (de) | 1994-07-11 | 1996-01-18 | Basf Ag | Schwefeloxide und deren Halogenderivate als elektrophiles Endgruppenverschlußreagens bei der elektrophilen Synthese von Polyaryletherketonen |
| DE4429107A1 (de) | 1994-08-17 | 1996-02-22 | Basf Ag | Formmassen aus Polyarylenethern und Copolyamiden |
| ES2116196B1 (es) * | 1995-02-27 | 1999-04-01 | Consejo Superior Investigacion | Procedimiento de obtencion de poliarilcetonas con grupos naftaleno en forma de particulas. |
| DE19526855A1 (de) * | 1995-07-22 | 1997-01-23 | Basf Ag | Verfahren zur Herstellung von Polyarylenethern mit Anhydridendgruppen |
| DE19545968A1 (de) | 1995-12-11 | 1997-06-12 | Basf Ag | Verfahren zur Reinigung von Polyarylenethern mit Wasser |
| GB2364319B (en) | 2000-07-06 | 2003-01-15 | Gharda Chemicals Ltd | Melt processible polyether ether ketone polymer |
| DE60236314D1 (en) | 2001-11-29 | 2010-06-17 | Ube Industries | Polyelektrolytzusammensetzungen |
| EP2456807B1 (de) * | 2009-07-24 | 2013-07-17 | Invista Technologies S.à.r.l. | Syntheseverfahren mit ionischen flüssigkeiten |
| GB0920590D0 (en) | 2009-11-25 | 2010-01-06 | Univ Leicester | New ionic liquids |
| FR3050993B1 (fr) * | 2016-05-09 | 2020-01-31 | Arkema France | Composition de poly-(aryl-ether-cetone) (paek) a faible taux de composes volatils et son utilisation dans un procede de frittage |
| KR102262524B1 (ko) | 2017-11-16 | 2021-06-07 | 한화솔루션 주식회사 | 폴리에테르케톤케톤 제조방법 및 이에 의해 제조된 폴리에테르케톤케톤 |
| TWI762758B (zh) * | 2018-01-22 | 2022-05-01 | 日商迪愛生股份有限公司 | 聚伸芳基醚酮樹脂及其製造方法以及成形品 |
| CN109608627B (zh) * | 2018-11-29 | 2021-09-28 | 山东凯盛新材料股份有限公司 | 聚醚酮酮的生产工艺 |
| CN109608626B (zh) * | 2018-11-29 | 2021-05-18 | 山东凯盛新材料股份有限公司 | 生产聚醚酮酮的工艺 |
| KR102250302B1 (ko) * | 2018-12-12 | 2021-05-07 | 한화솔루션 주식회사 | 개선된 폴리에테르케톤케톤 제조방법 및 이에 의해 제조된 폴리에테르케톤케톤 |
| CN114901722B (zh) * | 2019-11-27 | 2024-09-24 | 格哈达化工有限公司 | 聚醚酮酮及其制备方法 |
| CN111607077A (zh) * | 2020-06-24 | 2020-09-01 | 黄河三角洲京博化工研究院有限公司 | 一种聚酮的制备方法 |
| JP7655062B2 (ja) * | 2021-04-19 | 2025-04-02 | Dic株式会社 | ポリアリーレンエーテルケトン樹脂及びその製造方法、並びに成形体 |
| CN114773591B (zh) * | 2022-04-26 | 2023-10-13 | 中国科学技术大学先进技术研究院 | 聚呋喃二甲酰丁二胺的制备方法 |
| CN121270876A (zh) * | 2025-12-08 | 2026-01-06 | 吉林省中研高分子材料股份有限公司 | 聚醚酮酮制备方法、聚醚酮酮及用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57182321A (en) * | 1981-04-29 | 1982-11-10 | Ici Ltd | Manufacture of aromatic polyketone |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065205A (en) * | 1959-10-27 | 1962-11-20 | Du Pont | Aromatic polyketones and preparation thereof |
| GB971227A (de) * | 1962-05-21 | 1900-01-01 | ||
| US4052365A (en) * | 1962-11-06 | 1977-10-04 | Imperial Chemical Industries Limited | Manufacture of crystallizable polymeric phenylene ether sulphone ketones |
| GB1019226A (en) * | 1962-11-12 | 1966-02-02 | Ici Ltd | Polyketones |
| GB1086021A (en) * | 1964-01-22 | 1967-10-04 | Ici Ltd | Process for the production of aromatic polyketones |
| GB1164817A (en) * | 1965-08-04 | 1969-09-24 | Du Pont | Preparation of Aryl Polymers |
| NL6611019A (de) * | 1965-08-04 | 1967-02-06 | ||
| US3442857A (en) * | 1965-11-10 | 1969-05-06 | Du Pont | Boron trifluoride-hydrogen fluoride catalyzed synthesis of poly(aromatic sulfone) and poly(aromatic ketone) polymers |
| US3516966A (en) * | 1968-02-05 | 1970-06-23 | Du Pont | Polyketone copolymers |
| UST869003I4 (en) * | 1968-02-05 | 1969-12-16 | Defensive publication | |
| US3524833A (en) * | 1969-01-06 | 1970-08-18 | Du Pont | Polymers of hydroxy ketones and hydroxy sulfones |
| GB1340709A (en) * | 1970-06-10 | 1973-12-12 | Du Pont | Process for producing crystalline copolyketone films and insulated electrical conductors |
| DE2206836C2 (de) * | 1971-02-16 | 1983-03-17 | Raychem Corp., 94025 Menlo Park, Calif. | Polyketone und Verfahren zu ihrer Herstellung |
| DE2266022C2 (de) * | 1971-02-16 | 1987-11-19 | Raychem Corp., Menlo Park, Calif., Us | |
| BE789818A (fr) * | 1971-10-07 | 1973-04-06 | Du Pont | Composes de polycetal |
| BE791798A (fr) * | 1971-11-24 | 1973-05-23 | Du Pont | Polycetones |
| US3953400A (en) * | 1972-01-17 | 1976-04-27 | Raychem Corporation | Polyketones and methods therefor |
| US3791890A (en) * | 1972-02-18 | 1974-02-12 | Du Pont | Granualr polyketone preparation |
| US3956240A (en) * | 1973-07-12 | 1976-05-11 | Raychem Corporation | Novel polyketones |
| NL186451C (nl) * | 1973-07-12 | 1990-12-03 | Raychem Corp | Werkwijze ter bereiding van lineaire, kristallijne, in de smelt stabiele, aromatische polyketonen, alsmede gevormd voortbrengsel, dat geheel of ten dele onder toepassing van een dergelijk polyketon is vervaardigd. |
| US4239884A (en) * | 1975-08-11 | 1980-12-16 | Raychem Corporation | Process for isolation of solid polymers |
| CA1112393A (en) * | 1975-11-07 | 1981-11-10 | Klaus J. Dahl | Ketone and sulfone polymers |
| US4229564A (en) * | 1976-04-26 | 1980-10-21 | Raychem Corporation | Friedel-Crafts polymerization of monomers in the preparation of polyketones and polysulfones |
| US4247682A (en) * | 1979-05-07 | 1981-01-27 | Raychem Corporation | Aromatic ketone and sulfone polymers and process for the preparation thereof |
| US4356292A (en) * | 1981-05-20 | 1982-10-26 | The United States Of America As Represented By The Secretary Of The Air Force | Polyaromatic ether-keto-sulfones curable by Diels-Alder cycloaddition |
| US4356298A (en) * | 1981-05-20 | 1982-10-26 | The United States Of America As Represented By The Secretary Of The Air Force | Polyaromatic ether-ketone-sulfones containing 1,3-butadiene units |
| US4361693A (en) * | 1981-07-08 | 1982-11-30 | Raychem Corporation | Preparation of poly(arylene ketones) using thio- and dithiocarbonic acid derivatives |
| US4396755A (en) * | 1981-11-12 | 1983-08-02 | Imperial Chemical Industries Plc | Production of aromatic polyketones |
-
1984
- 1984-03-29 BR BR8406499A patent/BR8406499A/pt not_active IP Right Cessation
- 1984-03-29 AU AU28165/84A patent/AU566373B2/en not_active Ceased
- 1984-03-29 GB GB848408082A patent/GB8408082D0/en active Pending
- 1984-03-29 WO PCT/US1984/000465 patent/WO1984003891A1/en not_active Ceased
- 1984-03-29 JP JP59501652A patent/JPH0680113B2/ja not_active Expired - Lifetime
- 1984-03-30 EP EP87200609A patent/EP0243997B1/de not_active Expired - Lifetime
- 1984-03-30 AT AT84302190T patent/ATE41667T1/de not_active IP Right Cessation
- 1984-03-30 AT AT87200609T patent/ATE81518T1/de not_active IP Right Cessation
- 1984-03-30 ZA ZA842420A patent/ZA842420B/xx unknown
- 1984-03-30 DE DE8787200609T patent/DE3485955T2/de not_active Expired - Fee Related
- 1984-03-30 CA CA000450962A patent/CA1244996A/en not_active Expired
- 1984-03-30 EP EP84302190A patent/EP0124276B1/de not_active Expired
- 1984-03-30 DE DE8484302190T patent/DE3477389D1/de not_active Expired
- 1984-03-30 GB GB08408217A patent/GB2138433B/en not_active Expired
- 1984-04-01 IL IL71422A patent/IL71422A/xx unknown
- 1984-04-02 WO PCT/US1984/000493 patent/WO1984003892A1/en not_active Ceased
- 1984-04-02 EP EP84901676A patent/EP0138990A1/de not_active Withdrawn
-
1986
- 1986-07-18 GB GB08617558A patent/GB2179951B/en not_active Expired
-
1993
- 1993-11-09 JP JP5279385A patent/JPH06263871A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57182321A (en) * | 1981-04-29 | 1982-11-10 | Ici Ltd | Manufacture of aromatic polyketone |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8406499A (pt) | 1985-03-12 |
| ATE41667T1 (de) | 1989-04-15 |
| AU2816584A (en) | 1984-10-25 |
| WO1984003891A1 (en) | 1984-10-11 |
| ZA842420B (en) | 1985-06-26 |
| ATE81518T1 (de) | 1992-10-15 |
| EP0124276B1 (de) | 1989-03-22 |
| WO1984003892A1 (en) | 1984-10-11 |
| GB2179951B (en) | 1987-10-14 |
| EP0124276A2 (de) | 1984-11-07 |
| JPS60500961A (ja) | 1985-06-27 |
| GB8408082D0 (en) | 1984-05-10 |
| GB2138433A (en) | 1984-10-24 |
| AU566373B2 (en) | 1987-10-15 |
| EP0124276A3 (en) | 1985-12-27 |
| GB2138433B (en) | 1987-10-21 |
| EP0243997B1 (de) | 1992-10-14 |
| GB8408217D0 (en) | 1984-05-10 |
| GB8617558D0 (en) | 1986-08-28 |
| EP0243997A1 (de) | 1987-11-04 |
| CA1244996A (en) | 1988-11-15 |
| IL71422A (en) | 1987-12-20 |
| IL71422A0 (en) | 1984-07-31 |
| JPH06263871A (ja) | 1994-09-20 |
| DE3477389D1 (en) | 1989-04-27 |
| EP0138990A1 (de) | 1985-05-02 |
| DE3485955D1 (de) | 1992-11-19 |
| GB2179951A (en) | 1987-03-18 |
| DE3485955T2 (de) | 1993-05-19 |
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